Efficient synthesis of the C1-C9 fragment of 7,8-O-isopropylidene protected iriomoteolide 3a derivative

Abstract

An efficient and stereoselective synthesis of the C1-C9 moiety of the 7,8-O-isopropylidene protected iriomoteolide 3a derivative has been accomplished. In our strategy, we employed olefin cross-metathesis of the L-(+)-tartaric acid derivative (((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl) methoxy)(tert-butyl) diphenylsilane with a synthesized methyl (S)-3-methylhex-5-enate to successfully provide the correct olefin geometry of the desired fragment.